# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_anna1120_isat(da_final)_3
_database_code_depnum_ccdc_archive 'CCDC 1992506'
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2020-05-08 downloaded from the CCDC.
;
_audit_creation_date             2020-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
mrubin@ku.edu
radioanimation@rambler.ru
''
''
''
_chemical_name_common            ?
_chemical_name_systematic        
(E)-2-(4-ethylphenyl)-2-(3-oxoindolin-2-ylidene)acetonitrile
_chemical_formula_moiety         'C18 H14 N2 O'
_chemical_formula_sum            'C18 H14 N2 O'
_chemical_formula_weight         274.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.6798(2)
_cell_length_b                   11.21770(10)
_cell_length_c                   12.58050(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.8320(10)
_cell_angle_gamma                90
_cell_volume                     2845.53(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10550
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.1480
_cell_measurement_theta_min      4.3530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 8 0.1497
12 -3 0 0.0794
-7 -1 8 0.2002
5 7 1 0.0567
6 -1 -8 0.1739
3 7 0 0.0581
-3 -7 0 0.0444
-5 7 0 0.0559
-9 -5 0 0.0589

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.107
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.1585 0.2325 7.7719 0.1122 0.4774 0.8715
11.9560 -2.7998 0.3121 0.2282 0.9528 -0.2005
-6.9268 -0.5304 7.7318 0.3136 -0.1129 0.9428
5.3382 6.5430 0.7604 -0.9188 0.3238 0.2259
5.6406 -1.0313 -7.8988 -0.0938 0.0354 -0.9950
3.1931 7.0494 0.2017 -0.9704 0.1273 0.2051
-3.3364 -7.0415 -0.0008 0.9752 -0.1278 -0.1804
-4.7845 6.7979 0.3698 -0.8340 -0.4531 0.3147
-9.4562 -5.0697 0.1723 0.7938 -0.6078 -0.0232

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15274
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.345
_diffrn_reflns_theta_min         4.386
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    2.63    --  -41.72 -38.00-150.00   99
  2  ω    -87.00  -6.00   1.00    2.63    --  -41.72 125.00 150.00   81
  3  ω      6.00  83.00   1.00    2.63    --   41.72 -99.00  90.00   77
  4  ω      8.00  42.00   1.00    2.63    --   41.72  81.00 -41.72   34
  5  ω     30.00 106.00   1.00   10.53    --  112.00 -95.00  30.00   76
  6  ω     86.00 178.00   1.00   10.53    --  112.00  45.00-150.00   92
  7  ω     86.00 178.00   1.00   10.53    --  112.00  45.00-120.00   92
  8  ω     61.00 146.00   1.00   10.53    --  112.00 178.00   0.00   85
  9  ω    104.00 178.00   1.00   10.53    --  112.00 111.00 -30.00   74
 10  ω     36.00 109.00   1.00   10.53    --  112.00-111.00   0.00   73
 11  ω     30.00 106.00   1.00   10.53    --  112.00 -95.00   0.00   76
 12  ω     36.00 109.00   1.00   10.53    --  112.00-111.00 -30.00   73
 13  ω     40.00 141.00   1.00   10.53    --  112.00 -61.00   0.00  101
 14  ω     40.00 141.00   1.00   10.53    --  112.00 -61.00  60.00  101
 15  ω    103.00 178.00   1.00   10.53    --  112.00  77.00 120.00   75
 16  ω    104.00 178.00   1.00   10.53    --  112.00 111.00  30.00   74
 17  ω     36.00 140.00   1.00   10.53    --  112.00 -30.00-150.00  104
 18  ω    104.00 178.00   1.00   10.53    --  112.00 111.00 150.00   74
 19  ω     86.00 178.00   1.00   10.53    --  112.00  45.00 120.00   92
 20  ω     37.00 144.00   1.00   10.53    --  112.00 -74.00 -73.03  107
 21  ω   -114.00 -42.00   1.00    2.63    --  -41.72 -57.00 120.00   72
 22  ω      8.00  42.00   1.00    2.63    --   41.72  82.00  74.19   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0124894000
_diffrn_orient_matrix_UB_12      -0.1325839000
_diffrn_orient_matrix_UB_13      0.0202701000
_diffrn_orient_matrix_UB_21      0.0743605000
_diffrn_orient_matrix_UB_22      -0.0170833000
_diffrn_orient_matrix_UB_23      0.0508493000
_diffrn_orient_matrix_UB_31      -0.0123512000
_diffrn_orient_matrix_UB_32      0.0314582000
_diffrn_orient_matrix_UB_33      0.1130357000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2786
_reflns_number_total             2976
_reflns_odcompleteness_completeness 98.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0609P)²+0.9312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1106
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C12(H12), C7(H7), C13(H13), C4(H4), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41237(5) 0.46201(9) 0.27378(6) 0.0565(2) Uani 1 1 d . . . . .
N1 N 0.40639(5) 0.51583(9) 0.54459(7) 0.0449(2) Uani 1 1 d . . . . .
C8 C 0.42601(5) 0.62667(10) 0.51354(8) 0.0411(2) Uani 1 1 d . . . . .
C1 C 0.39895(5) 0.43609(10) 0.45993(8) 0.0398(2) Uani 1 1 d . . . . .
C2 C 0.41486(5) 0.50345(10) 0.36438(8) 0.0412(2) Uani 1 1 d . . . . .
C9 C 0.37857(6) 0.32118(10) 0.45900(8) 0.0410(2) Uani 1 1 d . . . . .
C11 C 0.35245(5) 0.26192(10) 0.54587(8) 0.0406(2) Uani 1 1 d . . . . .
N2 N 0.38536(7) 0.17951(11) 0.30100(9) 0.0672(3) Uani 1 1 d . . . . .
C3 C 0.43032(5) 0.62410(10) 0.40438(8) 0.0421(2) Uani 1 1 d . . . . .
C16 C 0.31518(6) 0.32477(10) 0.60670(9) 0.0441(3) Uani 1 1 d . . . . .
H16 H 0.307437 0.405721 0.593831 0.053 Uiso 1 1 calc R . . . .
C14 C 0.29976(6) 0.14746(10) 0.70754(9) 0.0466(3) Uani 1 1 d . . . . .
C10 C 0.38265(6) 0.24735(11) 0.36752(9) 0.0479(3) Uani 1 1 d . . . . .
C15 C 0.28956(6) 0.26840(11) 0.68595(10) 0.0473(3) Uani 1 1 d . . . . .
H15 H 0.264960 0.312313 0.725729 0.057 Uiso 1 1 calc R . . . .
C12 C 0.36151(7) 0.14016(11) 0.56558(10) 0.0510(3) Uani 1 1 d . . . . .
H12 H 0.385154 0.095758 0.524599 0.061 Uiso 1 1 calc R . . . .
C7 C 0.43888(7) 0.72953(11) 0.57521(10) 0.0524(3) Uani 1 1 d . . . . .
H7 H 0.436961 0.730890 0.648358 0.063 Uiso 1 1 calc R . . . .
C13 C 0.33586(7) 0.08444(11) 0.64515(10) 0.0540(3) Uani 1 1 d . . . . .
H13 H 0.342883 0.003200 0.657210 0.065 Uiso 1 1 calc R . . . .
C4 C 0.44586(7) 0.72686(12) 0.35329(11) 0.0553(3) Uani 1 1 d . . . . .
H4 H 0.448140 0.725854 0.280296 0.066 Uiso 1 1 calc R . . . .
C6 C 0.45470(8) 0.83011(13) 0.52304(13) 0.0638(4) Uani 1 1 d . . . . .
H6 H 0.463670 0.900574 0.562515 0.077 Uiso 1 1 calc R . . . .
C17 C 0.27196(8) 0.08444(13) 0.79401(12) 0.0612(3) Uani 1 1 d . . . . .
H17A H 0.229392 0.050311 0.759360 0.073 Uiso 1 1 calc R . . . .
H17B H 0.301333 0.018936 0.822524 0.073 Uiso 1 1 calc R . . . .
C5 C 0.45775(8) 0.83007(13) 0.41373(13) 0.0668(4) Uani 1 1 d . . . . .
H5 H 0.467870 0.900072 0.381298 0.080 Uiso 1 1 calc R . . . .
C18 C 0.26259(10) 0.15951(16) 0.88826(13) 0.0742(4) Uani 1 1 d . . . . .
H18A H 0.227640 0.216034 0.863428 0.111 Uiso 1 1 calc GR . . . .
H18B H 0.303009 0.201244 0.918552 0.111 Uiso 1 1 calc GR . . . .
H18C H 0.251126 0.109263 0.943045 0.111 Uiso 1 1 calc GR . . . .
H1 H 0.4047(7) 0.5008(14) 0.6117(13) 0.057(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2214(13) . ?
N1 C8 1.3905(14) . ?
N1 C1 1.3730(13) . ?
C8 C3 1.3962(14) . ?
C8 C7 1.3828(16) . ?
C1 C2 1.5165(14) . ?
C1 C9 1.3554(16) . ?
C2 C3 1.4545(16) . ?
C9 C11 1.4800(14) . ?
C9 C10 1.4355(15) . ?
C11 C16 1.3924(15) . ?
C11 C12 1.3933(16) . ?
N2 C10 1.1417(16) . ?
C3 C4 1.3917(16) . ?
C16 C15 1.3818(15) . ?
C14 C15 1.3904(17) . ?
C14 C13 1.3905(18) . ?
C14 C17 1.5138(16) . ?
C12 C13 1.3821(17) . ?
C7 C6 1.3807(19) . ?
C4 C5 1.377(2) . ?
C6 C5 1.390(2) . ?
C17 C18 1.502(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 110.74(9) . . ?
N1 C8 C3 110.13(9) . . ?
C7 C8 N1 128.34(10) . . ?
C7 C8 C3 121.51(11) . . ?
N1 C1 C2 106.47(9) . . ?
C9 C1 N1 127.40(9) . . ?
C9 C1 C2 126.07(9) . . ?
O1 C2 C1 125.34(11) . . ?
O1 C2 C3 129.60(10) . . ?
C3 C2 C1 105.02(8) . . ?
C1 C9 C11 125.77(9) . . ?
C1 C9 C10 118.82(10) . . ?
C10 C9 C11 115.40(10) . . ?
C16 C11 C9 121.05(10) . . ?
C16 C11 C12 117.88(10) . . ?
C12 C11 C9 121.00(10) . . ?
C8 C3 C2 107.60(9) . . ?
C4 C3 C8 120.59(11) . . ?
C4 C3 C2 131.80(10) . . ?
C15 C16 C11 120.84(10) . . ?
C15 C14 C13 117.58(11) . . ?
C15 C14 C17 122.05(11) . . ?
C13 C14 C17 120.36(11) . . ?
N2 C10 C9 173.42(13) . . ?
C16 C15 C14 121.44(11) . . ?
C13 C12 C11 120.94(11) . . ?
C6 C7 C8 116.85(12) . . ?
C12 C13 C14 121.30(11) . . ?
C5 C4 C3 118.21(12) . . ?
C7 C6 C5 122.51(13) . . ?
C18 C17 C14 116.21(12) . . ?
C4 C5 C6 120.31(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.869(16) 2.053(16) 2.8692(12) 156.1(14) 6_566 yes

_olex2_exptl_crystal_mounting_method 
'Mounted by acrylic glue on the glass stick'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.399
_oxdiff_exptl_absorpt_empirical_full_min 0.603
